Rent or Forfeit 14

Chapter 14: Maddison

Shaking atop a pair of Sarah's stiletto-heeled boots, Tommy waited nervously after ringing the doorbell. His trembling wasn’t just from the cold, though the December wind bit through his sheer tights as if they weren’t even there. The main reason was that he was waiting outside his long-term crush’s house, dressed like a woman. He glanced down at what he was wearing - a playsuit, as Monica had called it - and let out a long, drawn-out sigh. Though comfortable, the material was thin and rode high on his thighs, offering little protection against the elements. As a particularly strong gust of wind sent his bleached blonde hair cascading across his face, a surge of frustration welled up in Tommy, making him instantly regret agreeing to come.

Reaching up with his long red acrylic nails, Tommy carefully brushed away the strands of hair that had stuck to his glossy red lips. With his other hand, he pulled his little fur jacket tighter around his ever-slimming frame, trying to shield himself from the biting cold.

Finally, the door opened, releasing a comforting wave of warm air and revealing Maddison, dressed in a cute top and skirt, her piercing blue eyes locking onto his. “Hey, Tammy! I’m so glad you made it!” she squealed with excitement. “Come in! Come in!”

(See image 14.1)

"Hey, Maddy. Thanks for inviting me,” Tommy replied, carefully stepping into the hallway of the two-story townhouse on his incredibly tall and rather snug knee-high boots. When Maddison opened her arms for a hug, he stepped forward, and for just a millisecond, the world felt like a better place. With his head buried in her sweet-smelling auburn hair and the slightly unsettling sensation of his fake breasts pressing against Maddison’s real ones, Tommy melted into the embrace.

“Oh! Hi,” Maddison giggled as she felt Tommy gripping her tightly. Realizing he might be overdoing it, Tommy quickly released her and stumbled backwards, feeling a bit embarrassed.

Maddison closed the door and turned to look at Tommy, who was grinning nervously. “Wow, girl! Don’t you look glam today. Let me take a look at you,” she said, stepping back to take in his appearance from head to toe. “Caught a bit of sun, I see?” she added with a playful giggle.

“Err… Yeah… No… It’s not real,” Tommy stuttered, now feeling even more self-conscious. “I went with my sisters earlier, and they sprayed my whole body this colour.”

With the spray tan option coming out of the hat for the third time, Tommy had reluctantly chosen it, unable to imagine himself with pink hair and the humiliation that would bring. In the end, the trip to the tanning salon hadn’t been as bad as he’d feared. He was in and out in under an hour, and although his dark orangey-brown skin reminded him of his neglectful mother, he tried to push those thoughts aside, telling himself it was only temporary.

“Yeah, I kinda guessed,” Maddison replied, still giggling. “December isn’t typically sunbathing weather. But, hey! Sorry, I didn’t mean to make you feel uncomfortable. You look great,” she added, noticing that Tommy was staring down at the ground, shuffling awkwardly from one high-heeled boot to the other.

“Thanks,” Tommy replied, forcing a smile onto his bloated lips. He appreciated Maddison’s attempts to make him feel more comfortable, but internally, he felt emasculated and silly being there dressed as he was.

"Let me take your coat," Maddison offered, stepping forward. Tommy hesitated for a moment, still feeling the lingering chill from outside, but then handed it over. Maddison hung it on a hook next to the door before leading the crossdressed boy towards the kitchen. An awkward silence settled between them as they navigated the hallway, broken only by the loud clicks of Tommy’s heels, a sound that made him cringe, especially in contrast to the soft, almost silent padding of Maddison’s fluffy slippers.

“Are you hungry, Tammy? Mum made a cake earlier. It’s really good,” Maddison said as they reached their destination, her gaze fixed on him. She couldn’t help but be mesmerized by the transformation from the plain, grungy-looking boy she remembered from school into someone who now looked so polished and glamorous.

“Sure, I’ll take a slice,” Tommy replied, still hungry after the small piece of salmon and tiny portion of salad he’d had for dinner with his sisters.

“Coming right up. Go take a seat,” Maddison said cheerfully, turning to cut the cake.

(See image 14.2)

"Erm... thanks," Tommy replied, feeling awkward. He turned, pulled out a chair, smoothed out the fabric covering his panty-clad backside, and carefully sat down.

"So... I’ve got to ask," Maddison said after Tommy had crossed his legs and settled into the chair. "Have you always known you wanted to be a girl?" she blurted out while handing him a plate with a thin slice of cake.

Tommy was caught off guard by the question and looked up in surprise. "Oh! It’s not like that. I’m... It’s... umm... complicated," he stammered, trying to find the right words.

"Sorry, I didn’t mean to ask like that," Maddison said, sitting opposite while offering a reassuring smile. "I get it. Changing your whole life can’t be easy. Just know that I'm a good listener if you ever want to talk."

"That’s nice of you to say, Maddy, but really, it’s not what you think. I’m just dressing like this because my sisters are making me," Tommy replied, his frustration slipping through. Seeing the confusion on Maddison’s face, he sighed and lowered his head, realizing how absurd it must sound.

"You don’t have to make stuff up, Tammy. We've known each other like forever. You can be honest with me," Maddison said softly.

"I am," Tommy insisted, his eyes meeting hers, his long lashes fluttering.

Maddison raised an eyebrow. "So you’re telling me you dyed your hair blonde, got inch-long acrylic nails, shaped your brows, and got lip fillers - all because your sisters told you to? That sounds a bit far-fetched, don’t you think?"

"Yeah, I guess it does," Tommy sighed. "But it’s true. You’ve got to believe me. It’s like a game to them," he added, clearly flustered.

"And that outfit - who picked that out?" Maddison asked.

"Err... I did," Tommy admitted quietly. "But..."

"Stop," Maddison cut in. "You don’t need to feel embarrassed around me. Just be yourself. I saw the way you walked in here on those boots, you've defo been practising. Tell me you haven’t?"

Lost for words, Tommy just sighed. The cute girl in front of him - the one he’d always dreamed of making his girlfriend - was determined not to believe him. The evidence in front of her was just too convincing. "Can we talk about something else?" he asked, desperate to change the subject. "How’s Janae? Do you two still hang out? You were inseparable in school."

Sensing that it might be hard for Tommy to admit the truth, Maddison decided to drop her questioning, at least for now. "Of course, she’s my best friend. The plan is to meet her later."

“Later!” Tommy gasped. "You told her about me?"

"Of course, silly. I know you asked me not to tell anyone, but I don’t keep secrets from Janae," Maddison said with a sweet smile. "Don’t worry, she’s cool with it, and she’s dying to see you."

Tommy’s stomach twisted into knots as his blubbery lips parted in shock. "She’s coming here?" he asked, his voice rising with a nervous tremble.

"Yeah, she’ll be over in an hour or so," Maddison replied, nodding excitedly. "We’re thinking of having a few pre-drinks here, then heading into the city. Have you been out properly as Tammy yet?"

Tommy slowly shook his head, his pantyhosed legs beginning to tremble.

"Oh my god!" Maddison exclaimed, clapping her hands in excitement. "So tonight will be your first time. We’re going to have so much fun!"